(E,E)-farnesol
all-(E)-farnesol
Identification
| Name | (E,E)-farnesol |
| IUPAC | (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol |
| CAS Number | 106-28-5 |
| FDA UNII | X23PI60R17 |
| Molecular Formula | C15 H26 O |
| Molecular Weight | 222.37142000 |
| MDL Number | MFCD00002918 |
| Nikkaji Number | J5.049K |
| Beilstein | 1763926 |
Regulatory
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 97.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.88400 to 0.88900 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.356 to 7.397 |
| Refractive Index | 1.48700 to 1.49400 @ 20.00 °C. |
| Boiling Point | 283.00 to 284.00 °C. @ 760.00 mm Hg, 137.00 °C. @ 3.00 mm Hg |
| Vapor Pressure | 0.000370 mmHg @ 25.00 °C. (est) |
| Vapor Density | >1 ( Air = 1 ) |
| Flash Point | 230.00 °F. TCC ( 110.00 °C. ) |
| logP (o/w) | 5.314 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Strength | low |
| Odor Description |
at 100.00 %. subtle, green, floral
|
| Taste Description | green |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 6000 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 > 5000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| IFRA Critical Effect | Sensitization |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| Recommendation for (E,E)-farnesol flavor usage levels up to | 2.0000 ppm in the finished product. |
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Potential Uses
Natural Occurrence
Synonyms
2,6-
di-trans-farnesol
2,6,10-
dodecatrien-1-ol, 3,7,11-trimethyl-, (2E,6E)-
2,6,10-
dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)-
(2-trans,6-trans)-
farnesol
(2E,6E)-
farnesol
(E,E)-2,6-
farnesol
(E)-
farnesol
2-trans,6-trans-
farnesol
all-(E)-
farnesol
all-trans-
farnesol
trans, trans-
farnesol
trans,trans-
farnesol
(2E,6E)-3,7,11-
trimethyl-1-dodeca-2,6,10-trienol
(2E,6E)-3,7,11-
trimethyl-2,6,10-dodecatrien-1-ol
(E,E)-3,7,11-
trimethyl-2,6,10-dodecatrien-1-ol
trans,trans-3,7,11-
trimethyl-2,6,10-dodecatrien-1-ol
(2E,6E)-3,7,11-
trimethyl-dodeca-2,6,10-trien-1-ol
3,7,11-
trimethyldodeca-2-trans,6-trans,10-trien-1-ol
(2-trans,6-trans)-3,7,11-
trimethyldodeca-2,6,10-trien-1-ol
(2E,6E)-3,7,11-
trimethyldodeca-2,6,10-trien-1-ol
Info:
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
PubMed:
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed:
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
PubMed:
Essential oil composition and antimicrobial activities of two closely related species, Alpinia mutica Roxb. and Alpinia latilabris Ridl., from Peninsular Malaysia.
PubMed:
Gold(I) as an artificial cyclase: short stereodivergent syntheses of (-)-epiglobulol and (-)-4β,7α- and (-)-4α,7α-aromadendranediols.
PubMed:
Assessment of the antioxidant and antiproliferative effects of sesquiterpenic compounds in in vitro Caco-2 cell models.
PubMed:
[Tobacco--once a medicinal plant. Does it contain substances with medicinal properties?].
PubMed:
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
PubMed:
Chemical composition and in vitro antimicrobial and antioxidant activities of Citrus aurantium l. flowers essential oil (Neroli oil).
PubMed:
Characterization of essential oil from Citrus aurantium L. flowers: antimicrobial and antioxidant activities.
PubMed:
Determination of E,E-farnesol in Makgeolli (rice wine) using dynamic headspace sampling and stir bar sorptive extraction coupled with gas chromatography-mass spectrometry.
PubMed:
Study of trans-trans farnesol effect on hyphae formation by Yarrowia lipolytica.
PubMed:
β-ionone induces cell cycle arrest and apoptosis in human prostate tumor cells.
PubMed:
Engineered heterologous FPP synthases-mediated Z,E-FPP synthesis in E. coli.
PubMed:
Chemical composition and antifungal activity of Matricaria recutita flower essential oil against medically important dermatophytes and soil-borne pathogens.
PubMed:
Specific involvement of two amino acid residues in cis-nerolidol binding to odorant-binding protein 5 AlinOBP5 in the alfalfa plant bug, Adelphocoris lineolatus (Goeze).
PubMed:
A convergent stereocontrolled total synthesis of (-)-terpestacin.
PubMed:
Comparative study of the chemical composition and biological activities of Magnolia grandiflora and Magnolia virginiana flower essential oils.
PubMed:
Quorum sensing activity in Ophiostoma ulmi: effects of fusel oils and branched chain amino acids on yeast-mycelial dimorphism.
PubMed:
Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis).
PubMed:
Effect of exogenous administration of Candida albicans autoregulatory alcohols in a murine model of hematogenously disseminated candidiasis.
PubMed:
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed:
Drimenol: A versatile synthon for compounds with trans-drimane skeleton.
PubMed:
Influences of trans-trans farnesol, a membrane-targeting sesquiterpenoid, on Streptococcus mutans physiology and survival within mixed-species oral biofilms.
PubMed:
Evaluation of the mutagenicity of sesquiterpenic compounds and their influence on the susceptibility towards antibiotics of two clinically relevant bacterial strains.
PubMed:
Application of a multidimensional gas chromatography system with simultaneous mass spectrometric and flame ionization detection to the analysis of sandalwood oil.
PubMed:
Variation in volatile leaf oils of eleven eucalyptus species harvested from korbous arboreta (Tunisia).
PubMed:
The quorum-sensing molecule E,E-farnesol--its variable secretion and its impact on the growth and metabolism of Candida species.
PubMed:
Candida species extracellular alcohols: production and effect in sessile cells.
PubMed:
Production of geranylgeraniol on overexpression of a prenyl diphosphate synthase fusion gene in Saccharomyces cerevisiae.
PubMed:
Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.
PubMed:
Determination of the volatile composition in essential oil of Descurainia sophia (L.) Webb ex Prantl (Flixweed) by gas chromatography/mass spectrometry (GC/MS).
PubMed:
Recovery of E,E-farnesol from cultures of yeast erg9 mutants: extraction with polymeric beads and purification by normal-phase chromatography.
PubMed:
Flowerhead volatile oil composition of soilless culture-grown Chrysanthemum balsamita L.
PubMed:
Quantification approach for assessment of sparkling wine volatiles from different soils, ripening stages, and varieties by stir bar sorptive extraction with liquid desorption.
PubMed:
Overexpression of the gene encoding HMG-CoA reductase in Saccharomyces cerevisiae for production of prenyl alcohols.
PubMed:
Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography-quadrupole mass spectrometry for the determination of volatile compounds in wines.
PubMed:
Synthesis of cordiaquinones B, C, J, and K on the basis of a bioinspired approach and the revision of the relative stereochemistry of cordiaquinone C.
PubMed:
Secretion of E,E-farnesol and biofilm formation in eight different Candida species.
PubMed:
Morphogenesis control in Candida albicans and Candida dubliniensis through signaling molecules produced by planktonic and biofilm cells.
PubMed:
Characterization of (E,E)-farnesol and its fatty acid esters from anal scent glands of nutria (Myocastor coypus) by gas chromatography-mass spectrometry and gas chromatography-infrared spectrometry.
PubMed:
The rice (E)-beta-caryophyllene synthase (OsTPS3) accounts for the major inducible volatile sesquiterpenes.
PubMed:
Analysis of the essential oil of Grindelia discoidea.
PubMed:
Zoledronate inhibits endothelial cell adhesion, migration and survival through the suppression of multiple, prenylation-dependent signaling pathways.
PubMed:
Structure of the human mitochondrial monoamine oxidase B: new chemical implications for neuroprotectant drug design.
PubMed:
Determination of terpenes in tequila by solid phase microextraction-gas chromatography-mass spectrometry.
PubMed:
A soluble form of phosphatase in Saccharomyces cerevisiae capable of converting farnesyl diphosphate into E,E-farnesol.
PubMed:
Isolation and characterization of a monoamine oxidase B selective inhibitor from tobacco smoke.
PubMed:
Volatile constituents of redblush grapefruit (Citrus paradisi) and pummelo (Citrus grandis) peel essential oils from Kenya.
PubMed:
Monitoring farnesol-induced toxicity in tobacco BY-2 cells with a fluorescent analog.
PubMed:
Farnesol concentrations required to block germ tube formation in Candida albicans in the presence and absence of serum.
PubMed:
Responses to sex pheromone and plant odours by olfactory receptor neurons housed in sensilla auricillica of the codling moth, Cydia pomonella (Lepidoptera: Tortricidae).
PubMed:
Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors.
PubMed:
Comprehensive two-dimensional gas chromatography with flame ionization and time-of-flight mass spectrometry detection: qualitative and quantitative analysis of West Australian sandalwood oil.
PubMed:
Farnesol-DMPC phase behaviour: a (2)H-NMR study.
PubMed:
Quorum sensing in Candida albicans: probing farnesol's mode of action with 40 natural and synthetic farnesol analogs.
PubMed:
Detection of farnesyl diphosphate accumulation in yeast ERG9 mutants.
PubMed:
The maize gene terpene synthase 1 encodes a sesquiterpene synthase catalyzing the formation of (E)-beta-farnesene, (E)-nerolidol, and (E,E)-farnesol after herbivore damage.
PubMed:
Squalestatin 1-inducible expression of rat CYP2B: evidence that an endogenous isoprenoid is an activator of the constitutive androstane receptor.
PubMed:
African elephant sesquiterpenes. II. Identification and synthesis of new derivatives of 2,3-dihydrofarnesol.
PubMed:
Alendronate inhibits invasion of PC-3 prostate cancer cells by affecting the mevalonate pathway.
PubMed:
Quorum sensing in the dimorphic fungus Candida albicans is mediated by farnesol.
PubMed:
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
PubMed:
Metabolism of farnesyl diphosphate in tobacco BY-2 cells treated with squalestatin.
PubMed:
Synthesis and biological evaluation of the geometric farnesylated analogues of the a-factor mating peptide of Saccharomyces cerevisiae.
PubMed:
Effects of statins on vascular wall: vasomotor function, inflammation, and plaque stability.
PubMed:
Sex pheromone mimicry in the early spider orchid (ophrys sphegodes): patterns of hydrocarbons as the key mechanism for pollination by sexual deception.
PubMed:
Farnesyl anthranilate suppresses the growth, in vitro and in vivo, of murine B16 melanomas.
PubMed:
Pleiotropic effects of statins in atherosclerosis and diabetes.
PubMed:
Comparison of headspace techniques for sampling volatile natural products in a dynamic system.
PubMed:
Direct vascular effects of HMG-CoA reductase inhibitors.
PubMed:
Studies on the Synthesis of Elegan-Type Linear Diterpenes: The Efficient Total Syntheses of Eleganolone, Eleganolone Acetate, Elegandiol, Eleganonal, and Epoxyeleganolone
PubMed:
Lovastatin induces apoptosis by inhibiting mitotic and post-mitotic events in cultured mesangial cells.
PubMed:
Activators of the nuclear hormone receptors PPARalpha and FXR accelerate the development of the fetal epidermal permeability barrier.
PubMed:
Pharmacological control of the mevalonate pathway: effect on arterial smooth muscle cell proliferation.
PubMed:
Male sex pheromone of a giant danaine butterfly,Idea leuconoe.
PubMed:
Identification and characterization of geranylgeraniol kinase and geranylgeranyl phosphate kinase from the Archaebacterium Sulfolobus acidocaldarius.
PubMed:
Effects of farnesol on the thermotropic behavior of dimyristoylphosphatidylcholine.
PubMed:
Directed cell killing (apoptosis) in human lymphoblastoid cells incubated in the presence of farnesol: effect of phosphatidylcholine.
PubMed:
Differences in sensitivity to farnesol toxicity between neoplastically- and non-neoplastically-derived cells in culture.
PubMed:
Requirement for isoprenoid-dependent posttranslational modifications in the cell-cycle progression of human breast-cancer cells.
PubMed:
Growth inhibition of leukemia cell line CEM-C1 by farnesol: effects of phosphatidylcholine and diacylglycerol.
PubMed:
Chemical analysis of temporal gland secretions collected from an Asian bull elephant during a four-month musth episode.
PubMed:
The conformation of dolichol.
PubMed:
Chemosensory responses in two species of elephants to constituents of temporal gland secretion and musth urine.
PubMed:
Odor mimetism? : Key substances inOphrys lutea-Andrena pollination relationship (Orchidaceae: Andrenidae).
PubMed:
Total synthesis of chain-length-uniform dolichyl phosphates and their fitness to accept hexoses in the enzymatic formation of lipoglycans.
PubMed:
Constituents of temporal gland secretion of the African elephant,Loxodonta africana.
PubMed:
The Nasonov pheromone of the honeybeeApis mellifera L. (Hymenoptera, Apidae). Part II. Bioassay of the components using foragers.
PubMed:
Photosynthetic pigments of green sulfur bacteria. The esterifying alcohols of bacteriochlorophylls c from Chlorobium limicola.
PubMed:
Levels of short-chain fatty acids and of abscisic acid in water-stressed and non-stressed leaves and their effects on stomata in epidermal strips and excised leaves.
PubMed:
Hydrolysis and isomerization of trans,trans-farnesyl diphosphate by Andrographis tissue-culture enzymes.
PubMed:
Comparison between Biosynthesis of ent-Kaurene in Germinating Tomato Seeds and Cell Suspension Cultures of Tomato and Tobacco.
PubMed:
Detection and preliminary identification of endogenous antitranspirants in water-stressed Sorghum plants.
PubMed:
Biosynthesis of trans, trans- and cis, trans-farnesols by soluble enzymes from tissue cultures of Andrographis paniculata.
PubMed:
All-trans-farnesol: a naturally occurring antitranspirant?
PubMed:
Synthesis of cecropia juvenile hormone from trans,trans-farnesol.
PubMed:
Lipid metabolism in helminth parasites--VI. Synthesis of 2-cis,6-trans farnesol by Hymenolepis diminuta (Cestoda).